O-β-D-galactopyranosyl-(1-4)-β-D-xylopyranose | 100227-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-β-D-galactopyranosyl-(1-4)-β-D-xylopyranose
• 英文别名: β1,4-galactopyranosyl β-xylopyranoside；4-O-β-D galactopyranosyl-D-xylose；gaxilose；O⁴-β-D-Galactopyranosyl-β-D-xylopyranose；Galactose-beta-1,4-xylose；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(3R,4R,5R,6R)-4,5,6-trihydroxyoxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 100227-08-5
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: VCTBNHVCBSUQPG-YOUNRWHRSA-N

物化性质

• 沸点：
  613.7±55.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲醇 、 O-β-D-galactopyranosyl-(1-4)-β-D-xylopyranose 在 盐酸 作用下， 生成 methyl-(O⁴-β-D-galactopyranosyl-ξ-D-xylopyranoside)
  参考文献：
  名称：

  Structure of Corn Hull Hemicelluloses. Part IV. Partial Hydrolysis and Identification of 3-O-α-D-Xylopyranosyl-L-arabinose and 4-O-β-D-Galactopyranosyl-β-D-xylose ^1,2

  摘要：

  DOI：

  10.1021/ja01560a053
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 生成 O-β-D-galactopyranosyl-(1-4)-β-D-xylopyranose
  参考文献：
  名称：

  Xylose: The First Ambident Acceptor Substrate for Galactosyltransferase from Bovine Milk

  摘要：

  In the past few years the acceptor substrate specificity of beta 1,4-galactosyltransferase (GalT) from bovine milk has been investigated extensively by various groups. In each case, the beta 1,4-galactosylated products have been observed exclusively. Recently we reported on a frame-shifted recognition of modified acceptor substrates resulting in the formation of beta,beta-trehalose type disaccharides. In an extension to these investigations we have now found that xylose is recognized by the enzyme both in the normal and in the reverse orientation. Therefore galactosylation of xylose results in a mixture of beta 1,4- and beta 1,beta 1-galactopyranosyl xylopyranosides. Synthesis and preparation of both disaccharides and their behavior toward beta-galactosidase from E. coli are described. The results lead to some implications about the active site of GalT.

  DOI：

  10.1021/jo00101a038

文献信息

• Characterization of crystalline forms of gaxilose, a diagnostic drug
  作者：Federica Catti、Santos Hernández Gallego、Mónica Benito、Elies Molins、Francisco Marquillas Olóndriz

  DOI：10.1016/j.carres.2021.108232

  日期：2021.1

  non-invasive method for hypolactasia diagnosis. To date, no definitive guide for identifying gaxilose and distinguishing between crystalline forms is available. Data have been collected from a number of different analytical techniques in order to provide a full characterization of the compound and a simple method to discriminate between two solid forms.

  乳糖不耐症是由乳糖酶缺乏引起的病理，通常在肠细胞中产生，引起腹痛、腹胀、腹泻、胀气和恶心等症状。Gaxilose，即 4-O-β-D 吡喃半乳糖基-d-木糖，用作诊断药物，用于非侵入性诊断低乳糖酶症的方法。迄今为止，尚无确定加西糖和区分晶型的明确指南。为了提供化合物的完整表征和区分两种固体形式的简单方法，已经从许多不同的分析技术收集了数据。
• Stereoselective enzymatic galactosylation of C-glucosides
  作者：Luigi Panza、Pietro L. Chiappini、Giovanni Russo、Daniela Monti、Sergio Riva

  DOI：10.1039/a701747b

  日期：——

  The enzyme β-1,4-galactosyl transferase from bovine colostrum (GalT) is able stereoselectively to galactosylate C-glucosides (i.e. 1 and 4), precursors of stable glycoconjugate analogues, and a systematic investigation of the structural modifications at C-1 and/or C-5 of the glycosides that can be accepted by this enzyme has been undertaken, adding information to the currently accepted model of substrate binding into the GalT active site.

  牛初乳中的β-1,4-半乳糖基转移酶（GalT）能够立体选择性地半乳糖基化C-葡萄糖苷（即1和4）--稳定的糖苷类似物的前体--并对该酶可接受的糖苷的C-1和/或C-5结构修饰进行了系统研究，为目前公认的底物结合到GalT活性位点的模型增添了信息。
• 4-O-β-spD-Galactopyranosyl-spD-xylose: A new synthesis and application to the evaluation of intestinal lactase
  作者：Alfonso Rivera-Sagredo、Alfonso Fernández-Mayoralas、Jesús Jiménez-Barbero、Manuel Martín-Lomas、Daniel Villanueva、Juan J. Aragón

  DOI：10.1016/s0008-6215(00)90554-8

  日期：1992.4

  benzyl 2,3-O-isopropylidene-beta-D-xylopyranoside by glycosylation with 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl bromide and subsequent deprotection. Compound 2 was hydrolyzed in vitro by intestinal lactase; the Vmax was 25% of that with lactose and the Km was 370mM (cf. 27mM for lactose). Oral administration of 2 suckling rats led to urinary excretion of D-xylose which could be estimated colorimetrically

  由苄基2,3-O-异亚丙基-β-D-吡喃吡喃糖苷与2,3,4,6-四-O-苯甲酰基-糖基化制备4-O-β-D-半乳糖吡喃糖基-D-木糖（2）。 α-D-吡喃半乳糖基溴化物和随后的脱保护基。化合物2通过肠乳糖酶在体外水解；Vmax为乳糖的25％，Km为370mM（乳糖为27mM）。口服2只乳鼠导致D-木糖的尿排泄，可通过比色法估算。
• Xylose: The First Ambident Acceptor Substrate for Galactosyltransferase from Bovine Milk
  作者：Torsten Wiemann、Yoshihiro Nishida、Volker Sinnwell、Joachim Thiem

  DOI：10.1021/jo00101a038

  日期：1994.11

  In the past few years the acceptor substrate specificity of beta 1,4-galactosyltransferase (GalT) from bovine milk has been investigated extensively by various groups. In each case, the beta 1,4-galactosylated products have been observed exclusively. Recently we reported on a frame-shifted recognition of modified acceptor substrates resulting in the formation of beta,beta-trehalose type disaccharides. In an extension to these investigations we have now found that xylose is recognized by the enzyme both in the normal and in the reverse orientation. Therefore galactosylation of xylose results in a mixture of beta 1,4- and beta 1,beta 1-galactopyranosyl xylopyranosides. Synthesis and preparation of both disaccharides and their behavior toward beta-galactosidase from E. coli are described. The results lead to some implications about the active site of GalT.
• Structure of Corn Hull Hemicelluloses. Part IV. Partial Hydrolysis and Identification of 3-O-α-D-Xylopyranosyl-L-arabinose and 4-O-β-D-Galactopyranosyl-β-D-xylose ^1,2
  作者：R. Montgomery、F. Smith、H. C. Srivastava

  DOI：10.1021/ja01560a053

  日期：1957.2